CA2683956A1 - Quinolones et azaquinolones inhibant la prolyl hydroxylase - Google Patents
Quinolones et azaquinolones inhibant la prolyl hydroxylase Download PDFInfo
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- CA2683956A1 CA2683956A1 CA002683956A CA2683956A CA2683956A1 CA 2683956 A1 CA2683956 A1 CA 2683956A1 CA 002683956 A CA002683956 A CA 002683956A CA 2683956 A CA2683956 A CA 2683956A CA 2683956 A1 CA2683956 A1 CA 2683956A1
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- Prior art keywords
- oxo
- hydroxy
- methyl
- oxobutanoic acid
- compound according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 102000004079 Prolyl Hydroxylases Human genes 0.000 title abstract 2
- 108010043005 Prolyl Hydroxylases Proteins 0.000 title abstract 2
- 150000007660 quinolones Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 52
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 125000001188 haloalkyl group Chemical group 0.000 claims 8
- 238000000034 method Methods 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 239000003814 drug Substances 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 102000003951 Erythropoietin Human genes 0.000 claims 4
- 108090000394 Erythropoietin Proteins 0.000 claims 4
- 239000008280 blood Substances 0.000 claims 4
- 210000004369 blood Anatomy 0.000 claims 4
- 230000000694 effects Effects 0.000 claims 4
- 229940105423 erythropoietin Drugs 0.000 claims 4
- OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 206010020772 Hypertension Diseases 0.000 claims 2
- 206010021143 Hypoxia Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000002903 Thalassemia Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000004419 alkynylene group Chemical group 0.000 claims 2
- 238000011316 allogeneic transplantation Methods 0.000 claims 2
- 208000007502 anemia Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 230000033444 hydroxylation Effects 0.000 claims 2
- 238000005805 hydroxylation reaction Methods 0.000 claims 2
- 230000001146 hypoxic effect Effects 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- 230000000302 ischemic effect Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 230000000087 stabilizing effect Effects 0.000 claims 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 230000009885 systemic effect Effects 0.000 claims 2
- 238000002054 transplantation Methods 0.000 claims 2
- 230000029663 wound healing Effects 0.000 claims 2
- 238000002689 xenotransplantation Methods 0.000 claims 2
- FCBGADAOCBIFSG-UHFFFAOYSA-N 3-(3-carboxypropanoyl)-4-hydroxy-1-methyl-2-oxo-1,7-naphthyridine-6-carboxylic acid Chemical compound N1=C(C(O)=O)C=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=C1 FCBGADAOCBIFSG-UHFFFAOYSA-N 0.000 claims 1
- GBFBFKZVMZZMOO-UHFFFAOYSA-N 3-(3-carboxypropanoyl)-4-hydroxy-1-methyl-2-oxoquinoline-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=C1 GBFBFKZVMZZMOO-UHFFFAOYSA-N 0.000 claims 1
- SJZXVRXQWCLHRN-UHFFFAOYSA-N 3-(3-carboxypropanoyl)-4-hydroxy-1-methyl-2-oxoquinoline-7-carboxylic acid Chemical compound OC(=O)C1=CC=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=C1 SJZXVRXQWCLHRN-UHFFFAOYSA-N 0.000 claims 1
- VONBKRUVLFOEAW-UHFFFAOYSA-N 3-(3-carboxypropanoyl)-7,8-difluoro-4-hydroxy-1-methyl-2-oxoquinoline-6-carboxylic acid Chemical compound FC1=C(C(O)=O)C=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=C1F VONBKRUVLFOEAW-UHFFFAOYSA-N 0.000 claims 1
- JHZDQKFXZSDGEJ-UHFFFAOYSA-N 4-(1-benzyl-4-hydroxy-2-oxo-1,8-naphthyridin-3-yl)-4-oxobutanoic acid Chemical compound O=C1C(C(=O)CCC(=O)O)=C(O)C2=CC=CN=C2N1CC1=CC=CC=C1 JHZDQKFXZSDGEJ-UHFFFAOYSA-N 0.000 claims 1
- HTFCBCOEBHSEAY-UHFFFAOYSA-N 4-(1-benzyl-4-hydroxy-2-oxoquinolin-3-yl)-4-oxobutanoic acid Chemical compound O=C1C(C(=O)CCC(=O)O)=C(O)C2=CC=CC=C2N1CC1=CC=CC=C1 HTFCBCOEBHSEAY-UHFFFAOYSA-N 0.000 claims 1
- NGQMOMCWKBIGPS-UHFFFAOYSA-N 4-(1-benzyl-7,8-difluoro-4-hydroxy-2-oxoquinolin-3-yl)-4-oxobutanoic acid Chemical compound O=C1C(C(=O)CCC(=O)O)=C(O)C2=CC=C(F)C(F)=C2N1CC1=CC=CC=C1 NGQMOMCWKBIGPS-UHFFFAOYSA-N 0.000 claims 1
- APZBXINEKFBHMY-UHFFFAOYSA-N 4-(1-benzyl-7-bromo-4-hydroxy-2-oxoquinolin-3-yl)-4-oxobutanoic acid Chemical compound O=C1C(C(=O)CCC(=O)O)=C(O)C2=CC=C(Br)C=C2N1CC1=CC=CC=C1 APZBXINEKFBHMY-UHFFFAOYSA-N 0.000 claims 1
- ZDSHJJSUYHSJON-UHFFFAOYSA-N 4-(4-hydroxy-1-methyl-2-oxo-1,5-naphthyridin-3-yl)-4-oxobutanoic acid Chemical compound C1=CN=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=C1 ZDSHJJSUYHSJON-UHFFFAOYSA-N 0.000 claims 1
- RETQKIVXWLHCTB-UHFFFAOYSA-N 4-(4-hydroxy-1-methyl-2-oxo-1,7-naphthyridin-3-yl)-4-oxobutanoic acid Chemical compound N1=CC=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=C1 RETQKIVXWLHCTB-UHFFFAOYSA-N 0.000 claims 1
- DZVKKDNRFVPAPW-UHFFFAOYSA-N 4-(4-hydroxy-1-methyl-2-oxo-1,8-naphthyridin-3-yl)-4-oxobutanoic acid Chemical compound C1=CC=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=N1 DZVKKDNRFVPAPW-UHFFFAOYSA-N 0.000 claims 1
- VPMJBCORSOGLST-UHFFFAOYSA-N 4-(4-hydroxy-1-methyl-2-oxo-6-phenyl-1,7-naphthyridin-3-yl)-4-oxobutanoic acid Chemical compound C1=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=CN=C1C1=CC=CC=C1 VPMJBCORSOGLST-UHFFFAOYSA-N 0.000 claims 1
- YOPREHPEFDOGBH-UHFFFAOYSA-N 4-(4-hydroxy-1-methyl-2-oxo-6-phenyl-1,8-naphthyridin-3-yl)-4-oxobutanoic acid Chemical compound C1=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=NC=C1C1=CC=CC=C1 YOPREHPEFDOGBH-UHFFFAOYSA-N 0.000 claims 1
- LPEQEFOPSJSTKP-UHFFFAOYSA-N 4-(4-hydroxy-1-methyl-2-oxo-6-phenylquinolin-3-yl)-4-oxobutanoic acid Chemical compound C1=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=CC=C1C1=CC=CC=C1 LPEQEFOPSJSTKP-UHFFFAOYSA-N 0.000 claims 1
- MDAQYLRVTZKTHG-UHFFFAOYSA-N 4-(4-hydroxy-1-methyl-2-oxo-6-thiophen-2-yl-1,8-naphthyridin-3-yl)-4-oxobutanoic acid Chemical compound C1=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=NC=C1C1=CC=CS1 MDAQYLRVTZKTHG-UHFFFAOYSA-N 0.000 claims 1
- IUNXGLCEASABPB-UHFFFAOYSA-N 4-(4-hydroxy-1-methyl-2-oxo-6-thiophen-3-yl-1,8-naphthyridin-3-yl)-4-oxobutanoic acid Chemical compound C1=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=NC=C1C=1C=CSC=1 IUNXGLCEASABPB-UHFFFAOYSA-N 0.000 claims 1
- KEBLJXILKZQOQQ-UHFFFAOYSA-N 4-(4-hydroxy-1-methyl-2-oxo-7-phenylquinolin-3-yl)-4-oxobutanoic acid Chemical compound C=1C=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=CC=1C1=CC=CC=C1 KEBLJXILKZQOQQ-UHFFFAOYSA-N 0.000 claims 1
- TUKIBJBFQBPBIT-UHFFFAOYSA-N 4-(4-hydroxy-1-methyl-2-oxo-7-thiophen-2-yl-1,5-naphthyridin-3-yl)-4-oxobutanoic acid Chemical compound C=1N=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=CC=1C1=CC=CS1 TUKIBJBFQBPBIT-UHFFFAOYSA-N 0.000 claims 1
- VOIIANIAJYFQRM-UHFFFAOYSA-N 4-(4-hydroxy-1-methyl-2-oxo-7-thiophen-2-ylquinolin-3-yl)-4-oxobutanoic acid Chemical compound C=1C=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=CC=1C1=CC=CS1 VOIIANIAJYFQRM-UHFFFAOYSA-N 0.000 claims 1
- PEHGRZOSSVYJIL-UHFFFAOYSA-N 4-(4-hydroxy-1-methyl-2-oxo-7-thiophen-3-yl-1,5-naphthyridin-3-yl)-4-oxobutanoic acid Chemical compound C=1N=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=CC=1C=1C=CSC=1 PEHGRZOSSVYJIL-UHFFFAOYSA-N 0.000 claims 1
- NOPKKRQZPIYRIJ-UHFFFAOYSA-N 4-(4-hydroxy-1-methyl-2-oxo-7-thiophen-3-ylquinolin-3-yl)-4-oxobutanoic acid Chemical compound C=1C=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=CC=1C=1C=CSC=1 NOPKKRQZPIYRIJ-UHFFFAOYSA-N 0.000 claims 1
- GWLFXLKSLZHOBL-UHFFFAOYSA-N 4-(4-hydroxy-1-methyl-2-oxoquinolin-3-yl)-4-oxobutanoic acid Chemical compound C1=CC=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=C1 GWLFXLKSLZHOBL-UHFFFAOYSA-N 0.000 claims 1
- PTIPDKFKGRYNBP-UHFFFAOYSA-N 4-(4-hydroxy-6-iodo-1-methyl-2-oxo-1,8-naphthyridin-3-yl)-4-oxobutanoic acid Chemical compound C1=C(I)C=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=N1 PTIPDKFKGRYNBP-UHFFFAOYSA-N 0.000 claims 1
- QTSLKEWTNYUSLS-UHFFFAOYSA-N 4-(4-hydroxy-6-iodo-1-methyl-2-oxoquinolin-3-yl)-4-oxobutanoic acid Chemical compound C1=C(I)C=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=C1 QTSLKEWTNYUSLS-UHFFFAOYSA-N 0.000 claims 1
- ZAMAELQQNUDYGN-UHFFFAOYSA-N 4-(5,8-difluoro-4-hydroxy-1-methyl-2-oxoquinolin-3-yl)-4-oxobutanoic acid Chemical compound C1=CC(F)=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=C1F ZAMAELQQNUDYGN-UHFFFAOYSA-N 0.000 claims 1
- DCJKRKYLAIKIQM-UHFFFAOYSA-N 4-(5-bromo-4-hydroxy-1-methyl-2-oxoquinolin-3-yl)-4-oxobutanoic acid Chemical compound C1=CC(Br)=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=C1 DCJKRKYLAIKIQM-UHFFFAOYSA-N 0.000 claims 1
- GNZYLMGEWDHSRG-UHFFFAOYSA-N 4-(6-bromo-4-hydroxy-1-methyl-2-oxoquinolin-3-yl)-4-oxobutanoic acid Chemical compound C1=C(Br)C=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=C1 GNZYLMGEWDHSRG-UHFFFAOYSA-N 0.000 claims 1
- VGDSPTSAQNTGDA-UHFFFAOYSA-N 4-(6-cyclohexyl-4-hydroxy-1-methyl-2-oxo-1,8-naphthyridin-3-yl)-4-oxobutanoic acid Chemical compound C1=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=NC=C1C1CCCCC1 VGDSPTSAQNTGDA-UHFFFAOYSA-N 0.000 claims 1
- QMQPHLFJRRTUJR-UHFFFAOYSA-N 4-(6-cyclopentyl-4-hydroxy-1-methyl-2-oxo-1,8-naphthyridin-3-yl)-4-oxobutanoic acid Chemical compound C1=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=NC=C1C1CCCC1 QMQPHLFJRRTUJR-UHFFFAOYSA-N 0.000 claims 1
- FEKWXSVPTLHHCK-UHFFFAOYSA-N 4-(6-cyclopropyl-7,8-difluoro-4-hydroxy-1-methyl-2-oxoquinolin-3-yl)-4-oxobutanoic acid Chemical compound C1=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=C(F)C(F)=C1C1CC1 FEKWXSVPTLHHCK-UHFFFAOYSA-N 0.000 claims 1
- QATCZKHAJFAEST-UHFFFAOYSA-N 4-(7,8-dichloro-4-hydroxy-1-methyl-2-oxoquinolin-3-yl)-4-oxobutanoic acid Chemical compound ClC1=CC=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=C1Cl QATCZKHAJFAEST-UHFFFAOYSA-N 0.000 claims 1
- MUOXPOVTHZBCCK-UHFFFAOYSA-N 4-(7,8-difluoro-4-hydroxy-1-methyl-2-oxo-6-phenylquinolin-3-yl)-4-oxobutanoic acid Chemical compound C1=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=C(F)C(F)=C1C1=CC=CC=C1 MUOXPOVTHZBCCK-UHFFFAOYSA-N 0.000 claims 1
- FAWSLMNFZXXCSE-UHFFFAOYSA-N 4-(7,8-difluoro-4-hydroxy-1-methyl-2-oxoquinolin-3-yl)-4-oxobutanoic acid Chemical compound FC1=CC=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=C1F FAWSLMNFZXXCSE-UHFFFAOYSA-N 0.000 claims 1
- PXMYFGGKSJFUTN-UHFFFAOYSA-N 4-(7,8-difluoro-4-hydroxy-6-iodo-1-methyl-2-oxoquinolin-3-yl)-4-oxobutanoic acid Chemical compound FC1=C(I)C=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=C1F PXMYFGGKSJFUTN-UHFFFAOYSA-N 0.000 claims 1
- DXIRWIQKSNIGMX-UHFFFAOYSA-N 4-(7-bromo-4-hydroxy-1-methyl-2-oxo-1,5-naphthyridin-3-yl)-4-oxobutanoic acid Chemical compound BrC1=CN=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=C1 DXIRWIQKSNIGMX-UHFFFAOYSA-N 0.000 claims 1
- GZQNECCMESWBBW-UHFFFAOYSA-N 4-(7-bromo-4-hydroxy-1-methyl-2-oxoquinolin-3-yl)-4-oxobutanoic acid Chemical compound BrC1=CC=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=C1 GZQNECCMESWBBW-UHFFFAOYSA-N 0.000 claims 1
- GRYVYFQDXHKMOA-UHFFFAOYSA-N 4-(8-bromo-4-hydroxy-1-methyl-2-oxoquinolin-3-yl)-4-oxobutanoic acid Chemical compound C1=CC=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=C1Br GRYVYFQDXHKMOA-UHFFFAOYSA-N 0.000 claims 1
- PTNUYKWJXPHMIE-UHFFFAOYSA-N 4-(8-chloro-7-fluoro-4-hydroxy-1-methyl-2-oxoquinolin-3-yl)-4-oxobutanoic acid Chemical compound FC1=CC=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=C1Cl PTNUYKWJXPHMIE-UHFFFAOYSA-N 0.000 claims 1
- RYAZKPRQKDWVOY-UHFFFAOYSA-N 4-[3-(3-carboxypropanoyl)-4-hydroxy-1-methyl-2-oxoquinolin-6-yl]benzoic acid Chemical compound C1=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=CC=C1C1=CC=C(C(O)=O)C=C1 RYAZKPRQKDWVOY-UHFFFAOYSA-N 0.000 claims 1
- UCDZNCXFBWBDBT-UHFFFAOYSA-N 4-[3-(3-carboxypropanoyl)-4-hydroxy-1-methyl-2-oxoquinolin-7-yl]benzoic acid Chemical compound C=1C=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=CC=1C1=CC=C(C(O)=O)C=C1 UCDZNCXFBWBDBT-UHFFFAOYSA-N 0.000 claims 1
- YQIBBCNNLAFOBG-UHFFFAOYSA-N 4-[4-hydroxy-1-methyl-2-oxo-6-(oxolan-2-yl)-1,8-naphthyridin-3-yl]-4-oxobutanoic acid Chemical compound C1=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=NC=C1C1CCCO1 YQIBBCNNLAFOBG-UHFFFAOYSA-N 0.000 claims 1
- UPBRHIDKCQHDLT-UHFFFAOYSA-N 4-[4-hydroxy-1-methyl-2-oxo-6-(oxolan-3-yl)-1,8-naphthyridin-3-yl]-4-oxobutanoic acid Chemical compound C1=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=NC=C1C1CCOC1 UPBRHIDKCQHDLT-UHFFFAOYSA-N 0.000 claims 1
- MEVOFGCHWMIIFA-UHFFFAOYSA-N 4-[4-hydroxy-1-methyl-2-oxo-6-(trifluoromethyl)-1,8-naphthyridin-3-yl]-4-oxobutanoic acid Chemical compound C1=C(C(F)(F)F)C=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=N1 MEVOFGCHWMIIFA-UHFFFAOYSA-N 0.000 claims 1
- KZPKIWPQDMWYTK-UHFFFAOYSA-N 4-[4-hydroxy-1-methyl-2-oxo-7-(trifluoromethyl)-1,8-naphthyridin-3-yl]-4-oxobutanoic acid Chemical compound FC(F)(F)C1=CC=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=N1 KZPKIWPQDMWYTK-UHFFFAOYSA-N 0.000 claims 1
- FKGWGYJZENCLSV-UHFFFAOYSA-N 4-[4-hydroxy-1-methyl-2-oxo-7-(trifluoromethyl)quinolin-3-yl]-4-oxobutanoic acid Chemical compound FC(F)(F)C1=CC=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=C1 FKGWGYJZENCLSV-UHFFFAOYSA-N 0.000 claims 1
- NOWNKXMCVAWQOE-UHFFFAOYSA-N 4-[4-hydroxy-1-methyl-6-(oxan-2-yl)-2-oxo-1,8-naphthyridin-3-yl]-4-oxobutanoic acid Chemical compound C1=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=NC=C1C1CCCCO1 NOWNKXMCVAWQOE-UHFFFAOYSA-N 0.000 claims 1
- IFIDJMNUJFHFSS-UHFFFAOYSA-N 4-[4-hydroxy-1-methyl-6-(oxan-4-yl)-2-oxo-1,8-naphthyridin-3-yl]-4-oxobutanoic acid Chemical compound C1=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=NC=C1C1CCOCC1 IFIDJMNUJFHFSS-UHFFFAOYSA-N 0.000 claims 1
- SRWZDWZSTGIVCY-UHFFFAOYSA-N 4-[6-(2-fluorophenyl)-4-hydroxy-1-methyl-2-oxo-1,8-naphthyridin-3-yl]-4-oxobutanoic acid Chemical compound C1=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=NC=C1C1=CC=CC=C1F SRWZDWZSTGIVCY-UHFFFAOYSA-N 0.000 claims 1
- TWXKADPXTMSXEQ-UHFFFAOYSA-N 4-[6-(2-fluorophenyl)-4-hydroxy-1-methyl-2-oxoquinolin-3-yl]-4-oxobutanoic acid Chemical compound C1=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=CC=C1C1=CC=CC=C1F TWXKADPXTMSXEQ-UHFFFAOYSA-N 0.000 claims 1
- TZUKYOGAFJXCOU-UHFFFAOYSA-N 4-[6-(3-carboxypropanoyl)-5-hydroxy-8-methyl-7-oxo-1,8-naphthyridin-3-yl]benzoic acid Chemical compound C1=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=NC=C1C1=CC=C(C(O)=O)C=C1 TZUKYOGAFJXCOU-UHFFFAOYSA-N 0.000 claims 1
- ZGPHJWXDVGLPMW-UHFFFAOYSA-N 4-[6-(3-fluorophenyl)-4-hydroxy-1-methyl-2-oxo-1,8-naphthyridin-3-yl]-4-oxobutanoic acid Chemical compound C1=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=NC=C1C1=CC=CC(F)=C1 ZGPHJWXDVGLPMW-UHFFFAOYSA-N 0.000 claims 1
- SNACNZCDPIFFGM-UHFFFAOYSA-N 4-[6-(3-fluorophenyl)-4-hydroxy-1-methyl-2-oxoquinolin-3-yl]-4-oxobutanoic acid Chemical compound C1=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=CC=C1C1=CC=CC(F)=C1 SNACNZCDPIFFGM-UHFFFAOYSA-N 0.000 claims 1
- LEYLCDYLVZPLRI-UHFFFAOYSA-N 4-[6-(4-fluorophenyl)-4-hydroxy-1-methyl-2-oxo-1,8-naphthyridin-3-yl]-4-oxobutanoic acid Chemical compound C1=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=NC=C1C1=CC=C(F)C=C1 LEYLCDYLVZPLRI-UHFFFAOYSA-N 0.000 claims 1
- JVELYIINHUGAQE-UHFFFAOYSA-N 4-[6-(4-fluorophenyl)-4-hydroxy-1-methyl-2-oxoquinolin-3-yl]-4-oxobutanoic acid Chemical compound C1=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=CC=C1C1=CC=C(F)C=C1 JVELYIINHUGAQE-UHFFFAOYSA-N 0.000 claims 1
- IFYOZIRVWKVSKM-UHFFFAOYSA-N 4-[6-cyclopropyl-4-hydroxy-1-methyl-2-oxo-7-(trifluoromethyl)quinolin-3-yl]-4-oxobutanoic acid Chemical compound C1=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=CC(C(F)(F)F)=C1C1CC1 IFYOZIRVWKVSKM-UHFFFAOYSA-N 0.000 claims 1
- RGNFENLIMGXEPL-UHFFFAOYSA-N 4-[7,8-difluoro-4-hydroxy-1-methyl-2-oxo-6-(oxolan-2-yl)quinolin-3-yl]-4-oxobutanoic acid Chemical compound C1=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=C(F)C(F)=C1C1CCCO1 RGNFENLIMGXEPL-UHFFFAOYSA-N 0.000 claims 1
- SAPFJHPRRFUKIM-UHFFFAOYSA-N 4-[7,8-difluoro-4-hydroxy-1-methyl-2-oxo-6-(oxolan-3-yl)quinolin-3-yl]-4-oxobutanoic acid Chemical compound C1=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=C(F)C(F)=C1C1CCOC1 SAPFJHPRRFUKIM-UHFFFAOYSA-N 0.000 claims 1
- OVPREICYZRSPCE-UHFFFAOYSA-N 6-(3-carboxypropanoyl)-5-hydroxy-8-methyl-7-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(O)=C(C(=O)CCC(O)=O)C(=O)N(C)C2=N1 OVPREICYZRSPCE-UHFFFAOYSA-N 0.000 claims 1
- 102100037249 Egl nine homolog 1 Human genes 0.000 claims 1
- 101710111663 Egl nine homolog 1 Proteins 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- -1 perhaloalkyl Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Immunology (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US92528507P | 2007-04-18 | 2007-04-18 | |
| US60/925,285 | 2007-04-18 | ||
| US92774807P | 2007-05-04 | 2007-05-04 | |
| US60/927,748 | 2007-05-04 | ||
| PCT/US2008/004965 WO2008130600A2 (fr) | 2007-04-18 | 2008-04-16 | Quinolones et azaquinolones inhibant la prolyl hydroxylase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2683956A1 true CA2683956A1 (fr) | 2008-10-30 |
| CA2683956C CA2683956C (fr) | 2012-12-18 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2683956A Expired - Fee Related CA2683956C (fr) | 2007-04-18 | 2008-04-16 | Quinolones et azaquinolones inhibant la prolyl hydroxylase |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US8048894B2 (fr) |
| EP (1) | EP2142509B1 (fr) |
| JP (1) | JP2010524942A (fr) |
| AU (1) | AU2008241483B2 (fr) |
| CA (1) | CA2683956C (fr) |
| ES (1) | ES2442847T3 (fr) |
| WO (1) | WO2008130600A2 (fr) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2672656C (fr) * | 2006-12-18 | 2012-03-20 | Amgen Inc. | Composes de naphtalenone presentant une activite inhibititrice de prolyle hydroxylase, compositions et utilisations de ceux-ci |
| WO2008130600A2 (fr) * | 2007-04-18 | 2008-10-30 | Amgen Inc. | Quinolones et azaquinolones inhibant la prolyl hydroxylase |
| WO2009089547A1 (fr) | 2008-01-11 | 2009-07-16 | Fibrogen, Inc. | Dérivés d'isothiazole-pyridine en tant que modulateurs de l'activité du hif (facteur inductible par l'hypoxie) |
| US8324405B2 (en) | 2008-02-05 | 2012-12-04 | Fibrogen, Inc. | Chromene derivatives and use thereof as HIF hydroxylase activity inhibitors |
| US8759345B2 (en) | 2008-04-28 | 2014-06-24 | Janssen Pharmaceutica Nv | Benzoimidazoles as prolyl hydroxylase inhibitors |
| US8217043B2 (en) | 2008-08-20 | 2012-07-10 | Fibrogen, Inc. | Compounds and methods for their use |
| US8927591B2 (en) | 2008-11-14 | 2015-01-06 | Fibrogen, Inc. | Thiochromene derivatives as HIF hydroxylase inhibitors |
| NZ598242A (en) | 2009-07-17 | 2013-09-27 | Japan Tobacco Inc | Triazolopyridine compound, and action thereof as prolyl hydroxylase inhibitor and erythropoietin production inducer |
| EP2627638B1 (fr) | 2010-10-14 | 2017-07-12 | Immunahr AB | 1,2-dihydro-4-hydroxy-2-oxo-quinoléine-3-carboxanilides en tant qu'activateurs d'ahr |
| EP2670750B1 (fr) | 2011-02-02 | 2016-09-14 | Fibrogen, Inc. | Dérivés de naphthyridine en tant qu'inhibiteurs d'un facteur inductible par l'hypoxie |
| GB201102659D0 (en) | 2011-02-15 | 2011-03-30 | Isis Innovation | Assay |
| GB201113101D0 (en) | 2011-07-28 | 2011-09-14 | Isis Innovation | Assay |
| ES2689481T3 (es) | 2011-10-25 | 2018-11-14 | Janssen Pharmaceutica Nv | Formulaciones de sal de meglumina de ácido 1-(5,6-dicloro-1h-benzo[d]imidazol-2-il)-1h-pirazol-4-carboxílico |
| US20140256767A1 (en) * | 2011-10-31 | 2014-09-11 | The Broad Institute, Inc. | Direct inhibitors of keap1-nrf2 interaction as antioxidant inflammation modulators |
| JP5924984B2 (ja) * | 2012-03-06 | 2016-05-25 | 国立大学法人東京農工大学 | トリフルオロメチルピリジノン化合物およびその製造方法 |
| TW201410657A (zh) | 2012-08-02 | 2014-03-16 | Endo Pharmaceuticals Inc | 經取代胺基－嘧啶衍生物 |
| FR2994184B1 (fr) * | 2012-08-02 | 2017-12-08 | Biomerieux Sa | Procedes de fonctionalisation et reactifs utilises dans de tels procedes utilisant un anhydride aza-isatoique ou un de ses derives, molecules biologiques ainsi traitees et kits |
| AP2015008502A0 (en) * | 2012-12-24 | 2015-06-30 | Cadila Healthcare Ltd | Novel quinolone derivatives |
| CA2959688C (fr) | 2014-09-02 | 2024-02-27 | Sunshine Lake Pharma Co., Ltd. | Composes de quinolone et utilisation pour traiter les maladies liees au facteur pouvant induire l'hypoxie et/ou a l'erythropoietine |
| CN114302882A (zh) * | 2019-07-19 | 2022-04-08 | 威佛（国际）股份公司 | 用于治疗输血依赖型β-地中海贫血（tdt）的膜铁转运蛋白抑制剂 |
| TW202208355A (zh) | 2020-05-04 | 2022-03-01 | 美商安進公司 | 作為骨髓細胞觸發受體2促效劑之雜環化合物及使用方法 |
| AU2021267161A1 (en) | 2020-05-04 | 2022-12-08 | Amgen Inc. | Heterocyclic compounds as triggering receptor expressed on myeloid cells 2 agonists and methods of use |
| EP4146345A2 (fr) | 2020-05-05 | 2023-03-15 | Teon Therapeutics, Inc. | Modulateurs de récepteur cannabinoïde de type 2 (cb2) et leurs utilisations |
Family Cites Families (68)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US79726A (en) * | 1868-07-07 | Hbney bfllard | ||
| JPS5245474B2 (fr) | 1972-04-19 | 1977-11-16 | ||
| JPS5417754B2 (fr) | 1972-12-15 | 1979-07-02 | ||
| CA1022544A (en) | 1972-12-21 | 1977-12-13 | Yukiyasu Murakami | Process of preparing a heterocyclic acyl group-substituted cephalosporin derivative |
| JPS587637B2 (ja) | 1973-12-27 | 1983-02-10 | 住友化学工業株式会社 | シンキペニシリンノ セイホウ |
| AT328085B (de) | 1974-04-23 | 1976-03-10 | Sumitomo Chemical Co | Verfahren zur herstellung neuer penicilline |
| US4215123A (en) | 1979-05-07 | 1980-07-29 | American Home Products Corporation | Antisecretory 4-oxy-3-carboxy or cyano-1,2-dihydro-2-oxo-1,8-naphthyridine derivatives |
| US4468394A (en) | 1981-04-02 | 1984-08-28 | Eisai Co., Ltd. | Cephalosporin compounds |
| US4374138A (en) | 1981-11-13 | 1983-02-15 | Warner-Lambert Company | Antibacterial amide compounds, compositions, and methods of use |
| US4404201A (en) | 1981-11-13 | 1983-09-13 | Warner-Lambert Company | Cephalosporins |
| US4382089A (en) | 1982-03-02 | 1983-05-03 | Warner-Lambert Company | Antibacterial amide compounds, compositions thereof and methods of using them |
| US4710473A (en) | 1983-08-10 | 1987-12-01 | Amgen, Inc. | DNA plasmids |
| US5037826A (en) | 1986-10-15 | 1991-08-06 | Schering Corporation | 1-substituted naphthyridine and pyridopyrazine derivatives |
| SU1735288A1 (ru) | 1990-03-05 | 1992-05-23 | Харьковский государственный фармацевтический институт | Способ получени N-R-замещенных амидов 4-гидроксихинолон-2 карбоновой -3-кислоты |
| JP2988739B2 (ja) | 1990-04-16 | 1999-12-13 | 協和醗酵工業株式会社 | １，８−ナフチリジン−２−オン誘導体 |
| JPH0493592A (ja) | 1990-08-09 | 1992-03-26 | Nissan Motor Co Ltd | 回転蓄熱式熱交換器 |
| IL100917A0 (en) | 1991-02-16 | 1992-11-15 | Fisons Plc | Pyridinone and pyrimidinone derivatives,their preparation and pharmaceutical compositions containing them |
| US5155115A (en) | 1991-03-12 | 1992-10-13 | Kyowa Hakko Kogyo Co., Ltd. | Thienopyridine derivatives |
| DE4138820A1 (de) | 1991-11-26 | 1993-05-27 | Basf Ag | Chinolin-3-carbonsaeureamide, deren herstellung und verwendung |
| AU668694B2 (en) | 1991-12-19 | 1996-05-16 | Sanofi-Synthelabo | Saccharin derivative proteolytic enzyme inhibitors |
| DE4227747A1 (de) | 1992-08-21 | 1994-02-24 | Basf Ag | Heteroaromatisch kondensierte Hydroxypyridoncarbonsäureamide, deren Herstellung und Verwendung |
| US5502035A (en) | 1993-08-06 | 1996-03-26 | Tap Holdings Inc. | N-terminus modified analogs of LHRH |
| CA2138929A1 (fr) | 1993-12-30 | 1995-07-01 | Klaus Weidmann | Carboxamides heterocycliques substitues, leur preparation et leur utilisation comme composes pharmaceutiques |
| JPH07224040A (ja) | 1994-02-07 | 1995-08-22 | Fujisawa Pharmaceut Co Ltd | キノリン誘導体 |
| IL135495A (en) | 1995-09-28 | 2002-12-01 | Hoechst Ag | Intermediate compounds for the preparation of quinoline-converted amines - 2 - carboxylic acid |
| DE19746287A1 (de) | 1997-10-20 | 1999-04-22 | Hoechst Marion Roussel De Gmbh | Substituierte Isochinolin-2-Carbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel |
| CA2260499A1 (fr) | 1998-01-29 | 1999-07-29 | Sumitomo Pharmaceuticals Company Limited | Compositions pharmaceutiques pour le traitement de dommages ischemiques au cerveau |
| US6133285A (en) | 1998-07-15 | 2000-10-17 | Active Biotech Ab | Quinoline derivatives |
| GB9911047D0 (en) | 1999-05-12 | 1999-07-14 | Isis Innovation | Assay method and means |
| WO2001085732A1 (fr) | 2000-05-12 | 2001-11-15 | Kyorin Pharmaceutical Co., Ltd. | Derives de pyridobenzodiazine et procedes de preparation de ces derives |
| JP4272338B2 (ja) | 2000-09-22 | 2009-06-03 | バイエル アクチェンゲゼルシャフト | ピリジン誘導体 |
| WO2002076396A2 (fr) | 2001-03-23 | 2002-10-03 | Smithkline Beecham Corporation | Composes utiles en tant qu'inhibiteurs de kinase pour le traitement de maladies hyperproliferatives |
| CN100522946C (zh) | 2001-12-06 | 2009-08-05 | 法布罗根股份有限公司 | 低氧诱导因子(HIF)α的稳定化 |
| WO2004024693A1 (fr) | 2002-08-13 | 2004-03-25 | Shionogi & Co., Ltd. | Compose heterocyclique a activite inhibitrice de l'integrase du vih |
| US7019141B2 (en) | 2002-10-21 | 2006-03-28 | Irm Llc | Quinolones with anti-HIV activity |
| US7618940B2 (en) | 2002-12-06 | 2009-11-17 | Fibrogen, Inc. | Fat regulation |
| WO2004104000A1 (fr) | 2003-05-23 | 2004-12-02 | Japan Tobacco Inc. | Compose cyclique condense tricyclique et son utilisation medicale |
| WO2004103974A1 (fr) | 2003-05-23 | 2004-12-02 | Japan Tobacco Inc. | Compose 2-oxoquinoline substitue et utilisation medicale de celui-ci |
| BRPI0411055B1 (pt) | 2003-06-06 | 2018-08-21 | Fibrogen, Inc | Compostos de heteroarilas contendo nitrogênio. seus usos no aumento da eritropoietina endógena, composição farmacêutica que os compreende e método in vitro de inibição da atividade da enzima hidrolase |
| WO2005007192A2 (fr) | 2003-06-06 | 2005-01-27 | Fibrogen, Inc. | Cytoprotection |
| US8614204B2 (en) | 2003-06-06 | 2013-12-24 | Fibrogen, Inc. | Enhanced erythropoiesis and iron metabolism |
| JP4057972B2 (ja) * | 2003-07-25 | 2008-03-05 | 富士通株式会社 | 半導体装置の製造方法 |
| WO2005011696A1 (fr) | 2003-08-01 | 2005-02-10 | Fibrogen, Inc. | Inhibiteurs de 2-oxoglutarate dioxygenase en tant qu'inducteurs de gamma globine |
| EP1656376A1 (fr) | 2003-08-22 | 2006-05-17 | Avanir Pharmaceuticals | Derives de naphtyridine substitues servant d'inhibiteurs de facteur d'inhibition de la migration des macrophages et leur utilisation pour traiter des maladies humaines |
| US7378414B2 (en) | 2003-08-25 | 2008-05-27 | Abbott Laboratories | Anti-infective agents |
| DE602004024814D1 (de) | 2003-11-04 | 2010-02-04 | Merck & Co Inc | Substituierte naphthyridinonderivate |
| BRPI0507628A (pt) | 2004-02-11 | 2007-07-03 | Smithkline Beecham Corp | composto ou sal farmaceuticamente aceitável do mesmo, método de tratamento de uma infecção viral em um ser humano, uso de um composto composição farmacêutica, e, processo para a preparação de um composto |
| US7622582B2 (en) | 2004-05-17 | 2009-11-24 | Tibotec Bvba | Derivatives of 1-phenyl-benzofuro[3,2]pyridin-2(1H)-one |
| EP1849465A4 (fr) | 2005-02-18 | 2008-12-24 | Takeda Pharmaceutical | Agent de controle de la fonction du recepteur gpr34 |
| JP4792048B2 (ja) | 2005-03-02 | 2011-10-12 | ファイブロゲン インコーポレイティッド | チエノピリジン化合物およびその使用方法 |
| AR055319A1 (es) | 2005-03-17 | 2007-08-15 | Wyeth Corp | Derivados de isoquinoleina, composiciones farmaceuticas y usos |
| WO2006133391A2 (fr) | 2005-06-06 | 2006-12-14 | Fibrogen, Inc. | Methode amelioree de traitement de l'anemie |
| US8530404B2 (en) | 2005-06-15 | 2013-09-10 | Fibrogen, Inc. | Compounds and methods for treatment of cancer |
| WO2007038571A2 (fr) * | 2005-09-26 | 2007-04-05 | Smithkline Beecham Corporation | Antagonistes de la prolyl-hydroxylase |
| AU2006326662B2 (en) | 2005-12-09 | 2011-07-28 | Amgen Inc. | Quinolone based compounds exhibiting prolyl hydroxylase inhibitory activity, and compositions, and uses thereof |
| CN101420980A (zh) | 2006-02-16 | 2009-04-29 | 菲布罗根公司 | 治疗中风的化合物和方法 |
| WO2007101204A1 (fr) | 2006-02-27 | 2007-09-07 | Alcon Research, Ltd. | Méthode de traitement du glaucome |
| TW200808793A (en) | 2006-03-07 | 2008-02-16 | Smithkline Beecham Corp | Prolyl hydroxylase inhibitors |
| US20090176825A1 (en) | 2006-05-16 | 2009-07-09 | Fitch Duke M | Prolyl hydroxylase inhibitors |
| JO2934B1 (en) | 2006-06-23 | 2015-09-15 | سميث كلاين بيتشام كوربوريشن | Prolyl hydroxylase inhibitors |
| JP4876041B2 (ja) | 2006-08-30 | 2012-02-15 | 株式会社リコー | 画像形成装置 |
| US20090011051A1 (en) | 2006-09-28 | 2009-01-08 | Roth Mark B | Methods, Compositions and Articles of Manufacture for HIF Modulating Compounds |
| WO2008076425A1 (fr) | 2006-12-18 | 2008-06-26 | Amgen Inc. | Composés d'azaquinolone possédant une activité inhibitrice de prolyl hydroxylase, compositions et utilisations correspondantes |
| CA2672656C (fr) | 2006-12-18 | 2012-03-20 | Amgen Inc. | Composes de naphtalenone presentant une activite inhibititrice de prolyle hydroxylase, compositions et utilisations de ceux-ci |
| TW200845994A (en) | 2007-01-12 | 2008-12-01 | Smithkline Beecham Corp | N-substituted glycine derivatives: prolyl hydroxylase inhibitors |
| WO2008130600A2 (fr) | 2007-04-18 | 2008-10-30 | Amgen Inc. | Quinolones et azaquinolones inhibant la prolyl hydroxylase |
| WO2008137084A2 (fr) | 2007-05-04 | 2008-11-13 | Amgen Inc. | Diazaquinolones inhibant l'activité de la prolyl hydroxylase |
| ES2389063T3 (es) | 2007-05-04 | 2012-10-22 | Amgen, Inc | Derivados de tienopiridina y tiazolopiridina que inhiben la actividad prolil hidroxilasa |
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2008
- 2008-04-16 WO PCT/US2008/004965 patent/WO2008130600A2/fr active Application Filing
- 2008-04-16 AU AU2008241483A patent/AU2008241483B2/en not_active Ceased
- 2008-04-16 CA CA2683956A patent/CA2683956C/fr not_active Expired - Fee Related
- 2008-04-16 EP EP08743008.8A patent/EP2142509B1/fr active Active
- 2008-04-16 ES ES08743008.8T patent/ES2442847T3/es active Active
- 2008-04-16 JP JP2010504084A patent/JP2010524942A/ja not_active Ceased
- 2008-04-16 US US12/148,179 patent/US8048894B2/en active Active
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2011
- 2011-05-17 US US13/109,877 patent/US8349868B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US8048894B2 (en) | 2011-11-01 |
| US20090156605A1 (en) | 2009-06-18 |
| EP2142509A2 (fr) | 2010-01-13 |
| US8349868B2 (en) | 2013-01-08 |
| JP2010524942A (ja) | 2010-07-22 |
| CA2683956C (fr) | 2012-12-18 |
| US20110224248A1 (en) | 2011-09-15 |
| WO2008130600A3 (fr) | 2009-02-19 |
| AU2008241483A1 (en) | 2008-10-30 |
| WO2008130600A2 (fr) | 2008-10-30 |
| EP2142509B1 (fr) | 2013-12-04 |
| ES2442847T3 (es) | 2014-02-13 |
| AU2008241483B2 (en) | 2011-03-24 |
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